I’ve been prepping for my Jeopardy! moment since Grade 2

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The alarm clock on my BlackBerry reads 2:30 am.

My partner Paul is asleep beside me, whistling quietly as he exhales and grinning perhaps at some private joke.

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Paul is both a public servant and professional student. When not working, commuting, exercising or "playing hard" on his nights off, he rests contentedly as if in a catatonic stupor except for that low whistle.

I am not so different from Paul in most things. I have graduated law school and recently began to work at a downtown firm.

The long hours are a difficult adjustment. Really, I should be asleep. But lately I have grown increasingly restless, red- and bleary-eyed, like a man compelled to a higher calling.

Squinting by a dim night light, I am memorizing trivia. My objective is to earn a spot on Jeopardy!

That means trivia on the streetcar, trivia over lunch, on the toilet, before bed.

(All I have retained from this excellent work is that I apparently share my birthday with distinguished company: Harriet Tubman, Chuck Norris and Osama Bin Laden.)

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Outside of Jennings, Jeopardy! contestants do not become famous or earn fortunes. The money never was my mission.

My grandparents are first-generation immigrants from Italy. A former prisoner of war, my nonno trained to be a cobbler. My nonna peeled peaches at a baby-food factory, paid by the bushel.

My mother and father were elementary-school teachers. They brought their work home with them in the most beneficial sense – our basement was always cluttered with unused teaching materials, storybooks, laminated flashcards. These treasures fascinated me.

There was a humongous jigsaw puzzle of the United States, printed in dazzling colours with state capitals, landmarks and pictures of state symbols. Lying awake on weeknights – my bedtime was 8 p.m., right after the Jeopardy! telecast – I would review the map over and over in my mind, committing the images to memory, as if the silver sled dogs covering the Alaska puzzle piece might race out of my bedroom window as I slept.

My parents bought me actual toys and enrolled me in sports, but I got bored quickly. While most kids collected stickers or rocks, I collected facts.

By preschool, I had memorized the 12 birthstones. By the end of kindergarten I knew the 12 times table. A few months later, I was skipped into Grade 2.

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It was around that time that I became interested in Jeopardy! My father watched the show every night, barking answers at the TV from his throne-like armchair. As I came to join him, every question I got right (usually geography-related) brought his attention and pride. Dad would fill the commercial breaks with stories inspired by questions on the show. He was a loving man in a quiet way: warm if not expressive. Jeopardy! was our time.

By middle school I had memorized the British monarchs, by high school the Best Picture winners. I competed on my university's quiz bowl team for five years, the last year using an alias because I had already graduated and was no longer eligible.

It wasn't until law school, on a chance trip home, that I answered more Jeopardy! questions correctly than Dad did. Mom posted my score sheet on the fridge. Dad congratulated me, crestfallen, but with a gentle smile on his face.

For me, earning a spot on Jeopardy! would mean more than making partner, more than getting published.

I dog-ear pages of books. I keep a log of names and dates to research in my free time. I am always on Wikipedia. One day this information might appear on the show.

There is a multistep process for getting on Jeopardy! The first is an online test with 50 questions, each in a different category, and happens once a year. If you answer at least 35 correctly, your name is entered in a lottery for invitation to regional in-person tryouts, where you have to pass a second test and meet with the show's producers.

I have completed the online test three times. So far, no call has come. Last year, I answered 33 questions correctly – just below the cutoff. The years before that, I answered 31 and 30 questions correctly. Not bad by most measures, but not good enough to be on Jeopardy!

For a kid who has never been in a fight, these scores hit like a punch in the gut.

But now disappointment has strengthened my resolve. Two months ago, I began a new study regimen. I am more focused – or, as my partner says, more "obsessed" – than ever.

I am so near my goal that with hard work and a little luck (read: fewer opera questions) I might move up a weight class next year.

I am no Ken Jennings. But somehow the seeds of a humble upbringing, a curious nature and a family's pride have taken root in my brain and grown into a full-blown obsession with Jeopardy!

This is the only path I have ever known, and I have miles to go before I sleep. One day, my dad might watch me on TV. I see myself, in a dream, barking answers until my own sons can hear me.

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